| 1 | Sat 17 Aug 2019 | 6 4-1 v Pickering TownWorkington AFC 4-1 Pickering Town |
| 2 | Tue 20 Aug 2019 | 61-0 v TraffordTrafford 0-1 Workington AFC |
| 3 | Mon 26 Aug 2019 | 82-1 v Pontefract CollieriesWorkington AFC 2-1 Pontefract Collieries |
| 4 | Sat 31 Aug 2019 | 8 1-0 v City of LiverpoolCity of Liverpool 0-1 Workington AFC |
| 5 | Tue 3 Sep 2019 | 81-1 v ColneWorkington AFC 1-1 Colne |
| 6 | Sat 7 Sep 2019 | 81-1 v Runcorn LinnetsRuncorn Linnets 1-1 Workington AFC |
| 7 | Tue 10 Sep 2019 | 85-0 v Kendal TownWorkington AFC 5-0 Kendal Town |
| 8 | Sat 14 Sep 2019 | 80-2 v MossleyMossley 2-0 Workington AFC |
| 9 | Sat 21 Sep 2019 | 8 2-0 v WidnesWorkington AFC 2-0 Widnes |
| 10 | Sat 28 Sep 2019 | 65-1 v Ramsbottom UnitedWorkington AFC 5-1 Ramsbottom United |
| 11 | Sat 5 Oct 2019 | 62-2 v Marske UnitedMarske United 2-2 Workington AFC |
| 12 | Sat 2 Nov 2019 | 62-0 v Tadcaster AlbionWorkington AFC 2-0 Tadcaster Albion |
| 13 | Sat 16 Nov 2019 | 60-0 v MarineWorkington AFC 0-0 Marine |
| 14 | Sat 7 Dec 2019 | 64-2 v Ossett UnitedOssett United 2-4 Workington AFC |
| 15 | Sat 14 Dec 2019 | 64-0 v Prescot CablesWorkington AFC 4-0 Prescot Cables |
| 16 | Sat 21 Dec 2019 | 64-1 v Pickering TownPickering Town 1-4 Workington AFC |
| 17 | Thu 26 Dec 2019 | 64-1 v DunstonWorkington AFC 4-1 Dunston |
| 18 | Wed 1 Jan 2020 | 51-2 v Pontefract CollieriesPontefract Collieries 2-1 Workington AFC |
| 19 | Sat 4 Jan 2020 | 6 2-2 v TraffordWorkington AFC 2-2 Trafford |
| 20 | Sat 11 Jan 2020 | 63-0 v ColneColne 0-3 Workington AFC |
| 21 | Sat 18 Jan 2020 | 62-0 v Marske UnitedWorkington AFC 2-0 Marske United |
| 22 | Sat 25 Jan 2020 | 60-2 v Ramsbottom UnitedRamsbottom United 2-0 Workington AFC |
| 23 | Sat 1 Feb 2020 | 62-0 v Prescot CablesPrescot Cables 0-2 Workington AFC |
| 24 | Sat 8 Feb 2020 | 62-0 v Ossett UnitedWorkington AFC 2-0 Ossett United |
| 25 | Tue 18 Feb 2020 | 64-0 v DroylsdenDroylsden 0-4 Workington AFC |
| 26 | Sat 22 Feb 2020 | 66-0 v Kendal TownKendal Town 0-6 Workington AFC |
| 27 | Sat 29 Feb 2020 | 6 4-1 v ClitheroeWorkington AFC 4-1 Clitheroe |
| 28 | Sat 7 Mar 2020 | 63-1 v Brighouse TownWorkington AFC 3-1 Brighouse Town |
| 29 | Tue 10 Mar 2020 | 62-0 v MossleyWorkington AFC 2-0 Mossley |
| 30 | Sat 14 Mar 2020 | 64-2 v Tadcaster AlbionTadcaster Albion 2-4 Workington AFC |
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